There’s Something About Mary (1998)

This Farrelly Brothers comedy put Diaz on the map as a comic actress featuring the (errr…) hair-gel scene with Ben Stiller that brought tears from laughter. Who can forget all the priceless moments ranging from the zipper accidents to the flaming puppies?
Gangs of New York (2002)

It wasn’t Diaz’s prettiest costume and makeup design, but she was awfully feisty in the dirty streets of 19^th century New York City. She was a mean redhead who was dangerous with a knife, and oh yeah, got to hook up with Leonardo DiCaprio in a haystack – no big deal.
Shrek (2001)

Even though she was a cartoon, Shrek was arguably her most successful movie and franchise of her career. She paired up masterfully with Mike Myers as Princess Fiona, and made children and adults across the world smile to no end.
Any Given Sunday (1999)

Arguably one of, if not the, best performances for Cameron Diaz as she played a villain for the only time during her career—the hard nosed, greedy General Manager of the Miami Sharks. She was ruthless, cutthroat and scared the football players on the field. It’s one of the most underrated football movies of all time.
The Sweetest Thing (2002)

Aside from Selma Blair getting her mouth stuck on her boyfriend’s junk, there wasn’t much to watch in this movie. Diaz plays the love-struck Cristina Walters chasing Peter Donahue (played by Thomas Jane) taking a chance on true love. Yawn.
Charlie's Angels (2000)

We’re not supposed to take any movies directed by McG seriously, and Charlie’s Angels was no exception. Diaz, along with the rest of the girls, was ditzy and dim involved in a shallow plot even Michael Bay wouldn’t sniff.
What Happens in Vegas (2008)

A 28 percent approval rating on RottenTomatoes pretty much says it all, but it also says a lot about Diaz’s career choices within the last five years. She’s been settling for the same ditzy blonde role over and over again, and she’s got the range to do more.
The Holiday (2006)

Any Nancy Meyers movie spells danger, especially when the turtle necks and cashmere sweaters start showing up left and right. That said, it was moderately enjoyable watching Diaz and Jude Law interact because they’re such a beautiful couple…and have equally ridiculous incomes.